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Updated: Jun 30, 2025
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
A free-radical design featuring an intramolecular migration for a synthetically versatile alkyl-(hetero)arylation of
Dylan J Babcock1, Andrew J Wolfram1, Jaxon L Barney1
1The Pennsylvania State University, Department of Chemistry University Park PA 16802 USA nacsa@psu.edu.
Abstract:
A free-radical approach has enabled the development of a synthetically versatile alkyl-(hetero)arylation of olefins. Alkyl and (hetero)aryl groups were added concurrently to a full suite of mono- to tetrasubstituted simple alkenes (i.e., without requiring directing or electronically activating groups) for the first time. Key advances also included the introduction of synthetically diversifiable alkyl groups featuring different degrees of substitution, good diastereocontrol in both cyclic and acyclic settings, the addition of biologically valuable heteroarenes featuring Lewis basic nitrogen atoms as well as simple benzenes, and the generation of either tertiary or quaternary benzylic centers. The synthetic potential of this transformation was demonstrated by leveraging it as the key step in a concise synthesis of oliceridine, a new painkiller that received FDA approval in 2020.
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